


The Art of Losing

by CD (thecollective)



Category: Supernatural
Genre: Alternate Universe, F/M, First Kiss, M/M, Slow Burn
Language: English
Status: Completed
Published: 2016-02-01
Updated: 2016-02-01
Packaged: 2018-05-17 16:17:45
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 3
Words: 10,991
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/5877382
Author URL: https://archiveofourown.org/users/thecollective/pseuds/CD
Summary: <blockquote class="userstuff">
              <p>When Dean agrees to help Sam propose to Jess during a ski vacation with both of their families, he expects to feel somewhat out of place. What he doesn't see coming is his fast friendship with Jess' adopted brother, Castiel Novak. Both Dean and Cas are broken and a little bit lost, but Dean's starting to think that losing isn't all bad, if this thing with Cas is what he finds at the finish line.</p>
            </blockquote>





	1. Chapter 1

**Author's Note:**

> Thank you to my amazing artist, deanneedsyou! Creating a world of emotion around your art not only challenged but inspired me. I hope this piece reflects the beauty I found in your work.  
> You may find her original artwork here: http://themind-reels.livejournal.com/
> 
>  
> 
> This story is dedicated to Emily (@poteidia)
> 
> Part of the 2015 Supernatural ReverseBang Challenge
> 
> The title of the story comes from the Elizabeth Bishop poem, "One Art".

 

**_ _ **

 

**_***_ **

_The art of losing isn’t hard to master;_

_so many things seem filled with the intent_

_to be lost that their loss is no disaster._

_"One Art" by Elizabeth Bishop_

*******

Dean steps through the metal detector, his face passive, avoiding eye contact with the TSA agent in the blue uniform in order to get a better view of the planes out on the tarmac. Five hours inside one of those tin death machines and he only brought one book. Luckily, he never gets sick of Vonnegut.

Mumbling a curse under his breath, he slides into the bar nearest his boarding gate and orders two fingers of top shelf whiskey from the bartender.  He sets his arms flat on the bar and the wood is cold, even through the thick layer of his coat. In front of him, large windows reveal the icy runways of Kansas City Airport. The airport is enveloped in a storm, one that’s been brewing for days.

After knocking back the over-priced whiskey (which does nothing to calm his nerves, only causes him to feel tipsy and a little nauseous at the thought of the flight ahead of him), he heads to the waiting area near his boarding gate, bag and case in tow and watches as a man at the reception desk wearing a godawful red peacoat and black converse is told that there are no more seats on the plane. The man had been ticking his nails on the hard plastic one by one but stops, dropping his head to his chest and cursing under his breath when the airline receptionist furrows her brow and tells him the bad news. The flight is full. There are no seats left and no other flights out of Kansas until the Tuesday morning. The storm is coming in too fast. Dean has the decency to feel guilty for a moment, before focusing in on the loud speaker overhead.

“Rows 34 through 43 are now boarding. Rows 34 through 43, now boarding Flight 197, Kansas City to Sun Valley, Idaho. Last call for Flight 197, all rows, to Sun Valley.”

Dean turns away from the reception desk and the disappointed stranger, tosses his dark green duffle over one shoulder, his guitar case over the other, and glares at the lady checking boarding passes for no reason other than he really, really doesn’t want to fly tonight. The worker doesn’t say anything, doesn’t even look up, only grunts when Dean shoves his I.D. and ticket under the steward’s nose. Dean gets it. He’s tired, too. The gadget in the woman’s hand beeps when the red laser meets the correct sequence of lines and numbers on the pass and Dean sucks in a breath. Here we go, he thinks, grinding his teeth. Dean hates flying, especially flying alone, but he made a promise to his brother **.**  He follows the crowd through the carpeted, metal tube onto the airplane, shuffled through by silent strangers who don’t look up from their phones or feet. Plastering on a confident swagger he doesn’t feel, Dean pushes through tightly packed rows filled with tuned-out business women, wandering young tourists, haggard fathers and sullen teens until he finds seat 42G, near the back of the plane, against a window. The overhead compartments all around him are already full, and he is forced to hand off his guitar and duffel bag to the airline employee. The flight attendant moves down the aisle until he comes to an open overhead and shoves Dean’s guitar case and bag inside before closing the hatch with a huff of exertion. Dean watches and then sinks into his seat, finally, the adrenaline of boarding and the fear of taking off coursing through him until he forces himself to sit back and focus on the music in his headphones.

Closing his eyes, Dean evens out his breathing, allowing himself to indulge in the wax and wane of Chopin’s piano and violin duet thrumming an easy rhythm in the space between his ears. When the plane begins to move, he’s on track number 4. His shallow breaths come a little shorter, but Dean doesn’t open his eyes, only grips the armrest tighter, knuckles white and rigid against gravity. Only when the jet has pushed off solid terra to ascend the darkened sky does Dean allow himself to relax.

“Dean!” He hears his name only a half second before Sam grabs his guitar case and wraps his arm around his brother. “It’s so good to see you, man. Happy birthday!”

“My birthday was last week, dude.”

“Still counts. Hasn’t been seven days, yet.”

“Good to know you’re still a huge dork,” Dean answers back, a smile already forming on his lips. He has missed his little brother. “Where’s Jess? How’s plans comin’ along? Her family make it here yet?”

Dean rapid fires questions at Sam and watches him turn an interesting shade of pink before sputtering out a weak, “No one’s here but you and I didn’t even think you were going to actually ever show up. The damn storm has her brother stranded on his layover til God knows when and her parents are stuck in Chicago until morning. I don’t know how you made it through, but I’m glad that you did,” Sam clasps his brother’s shoulder. “I need you here with me. I _want_ all of them here, but you. You, I need,” he finishes in a low, conspiratorial voice that makes Dean roll his eyes in mock annoyance.

“Alright, alright, princess. I’m here. Let’s find your frog.”

“I am no frog, Dean Winchester,” Jess says from behind him and Dean can’t help the grin that breaks out across his face. His brother is a lucky man. Jess is smart and kind and never begrudges Sam the way they grew up (not great) or judges him for any of his demons (few and far between, but there). The best thing about Sam moving to California to get his law degree at Stanford besides the goddamn letters behind his name is definitely Jess.

“Jessica Moore, as I live and breathe,” Dean drawls, tugging her into a tight hug. “You find some sense and decide to pick the cute brother, yet?”

“Oh, Dean, I already have,” Jess winks as she grabs Sam’s hand. Dean shakes his head, amused at the blush that rises from underneath his brother’s collar when Jess kisses him on the cheek.

“Just checkin’,” he jokes, grabbing his duffle bag, which Sam swiftly snatches from his hand and tosses over his own shoulder to rest next to Dean’s guitar. Dean smothers a grin and pushes the button on the elevator. “Your family’s stuck on the other side of this storm, I hear?”

“Yeah,” she sighs. “I’m wondering why the hell Sam and I decided to get our families together in the dead of winter instead of travelling during Christmas, when the weather was actually decent across the midwest,” Jess admits, pushing into the elevator as soon as the doors open, making way for Sam and Dean. “The snow is going to be amazing tomorrow, though.”

Dean nods in agreement, watching the numbers tick up from L to 1 and then a rapid succession until they arrive at the 6th floor.  

“Are you guys on the same floor as me?” he asks.

“We’re all on six,” Jess grins. “We booked four rooms for six nights and then a room for Bobby and Ellen on the last night. They’re driving up on Saturday, right babe?”

Sam’s hair flops in agreement. “Yup. The whole family will be here for dinner, except Jo, who’s stuck in winter session back at school and can’t get free. It’s gonna be great, having everyone together. I can’t wait for you to meet Bobby and Ellen, babe. They’re gonna love you,” Sam rushes to add. Dean stifles a smile. His baby brother is nervous. How adorable.

“Bobby and Ellen are gonna love anyone who’ll put up with this gigantor for more than thirty seconds,” Dean takes the time to ruffle his brother’s hair and tries not to dwell on the fact that he needs to reach up to do so.

When they arrive at Dean’s room, Sam and Jess make him promise to join them for dinner, and then Jess’ phone rings, flashing a picture Dean cannot make out and she excuses herself, wandering down the hall, murmuring as she heads into the room she and Sam are sharing, only three doors down. Sam shrugs and turns to follow Jess and Dean shakes his head in mock disbelief before lifting a hand in solidarity and stepping into the empty room.

“Are you trying to get me drunk, Dean Winchester?” Jess giggles before smoothly downing the shot of whiskey in front of her. Dean smirks and tosses back his own drink, while Sam watches them, face placid, a glass of sparkling water in his hands.

“Is it working?” Dean asks, licking his lips. He’s watching the bartender with the ginger beard over Jess’ shoulder, trying not to make it obvious and failing spectacularly.

“Stop flirting with my girlfriend, Dean.”

“Shuddup, Sammy,” Jess grins and Dean barks out a laugh until she catches his eye and then turns to look behind her.

“And are you dating anyone right now, Dean?” She asks, arching a brow. “It’s been ages since Lisa and even longer since Adam.”

“Jess…”

“What? The bartender’s cute, is all.” She shrugs at Sam, who is now looking at her as if she just asked if Dean likes to bottom or top.

“Leave him alone,”Sam warns.

Dean snorts at his brother's discomfort. “It's fine, Sam. Not like she asked…”

“Okay please, stop. God, I hate you both,” he adds, grumbling under his breath about curses and his lot in life and some other shit that Dean can’t make out.

Dean turns back to Jess, who is circling an empty glass with her fingertip, feigning innocence and not making eye contact. He sighs. “Honestly? I just expanded the bakery, hired three new people and took on two hipster weddings for Valentine’s weekend. Unless the person of my dreams shows up to sweep me off my feet, I am off the market for the foreseeable future. I don’t have time for a relationship,” he finishes hoping to God that Jess is too drunk to hear the high-pitched desperation in his voice. He knows Sam heard, because his brother is looking at him, brows raised, with burgeoning puppy dog eyes. Luckily, Jess focuses on the hipster weddings and gets Dean talking about the different berry crumble pies he plans to bake in mason jars for the barn motif and before long, they’re ordering dutch apple a la mode at the bar instead of whiskey and the red-bearded bartender is eyeballing Dean from across the room, which Dean ignores in favor of making Jess snort milk out of her nose.

The sweets from the night before offset Dean’s hangover (Jess isn’t so lucky), and so Dean wakes early to hit the slopes. He tries to convince Sam to come with him, but Sam opts to sleep in and wait with Jess for her brother to arrive.

“He slept on the floor at Kansas International, dude,” Sam explains over the phone. “We’re gonna get him to his room and take him for a drink, just like we did for you.”

“I thought he wasn’t her _real_ brother.”

“They grew up together. Her parents took him in when his passed away. Come on Dean, I told you all this.”

“Yeah, yeah. What’s his name, again? Chaz? Chris?”

“Cas. It’s Cas.”

“Right, Cas.”

“Castiel Novak.”

“Weird name.”

“Come on, Dean.”

“What?”

“Be nice. He’s family.”

“I’m always nice.”

“Not _that_ nice, Dean.”

“Watch it, nerd.”

Later, on the slopes, when the snow sits quiet and shining in the early morning sun, Dean flies down the black diamond trail of Bald Mountain, face tucked into his chest, goggles cold against his cheeks. The breeze buzzes all around him, the _whoosh_ of wind and snow drowning out the silence of his solitude. On the ice, his vision sharpens, focusing on traversing the path in front of him, avoiding the trees around him and enjoying the outdoors all around him. He forgets about his empty bed back in Lawrence, the ache in his chest every time he thinks about his brother living two thousand miles away, the late nights at the bakery, heading home to a dark house and cold take-out that he eats in front of the television. He doesn’t think about the one night stands, rough hands and forgotten names, or the loneliness that has settled in his gut, taking root and planting seeds of doubt that make him unsure whether or not he will ever find anyone who is willing to break through to his core. Instead, Dean hunkers down on his haunches, pushing his speed up and zooms toward the twin orange flags that he spots in the distance until he’s panting with exertion and sweaty underneath his ski gear.   

Sam meets him outside of the lodge, on the steps leading to the lobby, where couches and chairs surround a large fireplace that allows guests to lounge and share in the warmth. “Good run?” He asks, but doesn’t wait for an answer before he continues on. “Jess’ family is here. Her parents made it in and so did Cas and we’re going to meet in the restaurant for lunch at noon and then they want to hit the bunny slopes and will you please, please, please come with us?” His brother doesn’t take a breath until the request is out and Dean realizes that Sam’s nerves must be on edge for him to ask Dean to go to the bunny slopes after a dawn run. Dean is tired and all he wants to do is go take a shower and not deal with people on his first goddamn vacation since he bought the bakery. But Sam is asking for something and he hasn’t asked Dean for anything, not since he moved to California, and it feels good to be needed. This week might be Dean’s vacation, but he’s only here because of Sam. So, Dean nods with as much enthusiasm he can muster and begs off meeting the family until after he’s run up to his room and changed for lunch. Back on the 6th floor, Dean plugs his iPhone into the speaker dock and Joni Mitchell’s _Blue_ blasts through the silence of his room as he enjoys a short, steaming shower. He tosses on a pair of blue jeans, a grey shirt and a green flannel overshirt that brings out the color of his eyes. After a cursory glance in the mirror and a quick dab of hair gel, Dean grabs his phone, wallet and room key, pulls on his socks and boots and heads back down to the lobby to meet up with the Moores.

It's actually the Moores and one Novak, Dean reminds himself as he walks into the lobby. He moves toward his brother and Jess who are sitting in front of the fireplace with a man he cannot place, but somehow, recognizes. The three of them look so snug and comfortable with one another, Dean pushes down the thought that he’s the outsider here, the one who never visits. The one who the rest of the family hasn’t met. The one who can’t seem to get, _and keep_ , it together. Well, he’s at least met Jess, which is more than Bobby and Ellen can say.

Sam looks up and smiles at Dean’s approach, but doesn’t miss a beat in the conversation. Jess has her arm flung around a man who is decidedly _not_ Sam, laughing with her head thrown back, eyes closed, full on _guffawing_ at something Sam said. In sharp contrast to Jess, the man sitting with them has dark hair and a soft, pensive smile that doesn’t so much move his mouth as it does make his eyes light up. And what gorgeous eyes, they are, Dean can’t help but think. Blue as the icy pond right outside the lodge, but as soon the man turns his gaze on him, Dean freezes.

“Hey...hey.” He lifts his arm in an aborted wave because he's not twelve, and suddenly it hits him where he know this guy from.

“Dean, come sit for a minute. This is my brother, Castiel. Cas, this is Sam’s older brother, Dean,” Jess says, her hand still flung across Cas’ shoulder.

“Wow, I mean, yeah. I met, I mean, I saw, I mean...shit. You were at the airport. When I flew out. I saw your red coat.” He motions to the bright crimson peacoat Cas has pulled tightly around him. “The coat and Converse? I noticed them.” A warm blush rises up the back of Dean’s neck when he realizes his brother is watching him stammer through this first introduction to Jess’ brother. “Flight 197 out of Kansas City on Monday?” Dean watches the recognition finally spark behind Cas’ eyes. It is quickly replaced by the annoyed glare of a man who slept on an airport floor less than 24 hours ago. “I got the last ticket.” Dean grimaces. “Sorry.”

Cas’ features smooth out and he appraises Dean. For a moment, he feels exposed, nerves raw as Cas sizes him up, eyes drawing across Dean’s features, taking in all of him. Then Cas smiles, reaching out a hand for Dean to shake and Dean feels like the fucking sun came out, warming him up from the inside, out.

“No need to apologize. All’s fair in love and airline travel,” Cas jokes.

“Um, okay. So,” Jess interrupts. “We are going to go up the mountain in an hour. First, we eat a light lunch, and then Dean’s gonna give Cas a lesson, right, Dean?” Dean gives a perfunctory nod. He’d promised Sam he’d do a quick ski lesson for Jess’ brother as part of this whole _thing_ Sam has planned before he pops the big question. “Cas, you go change and meet us at the buffet.”

“Yes ma’am,” Cas mock salutes and Dean grins. Cas looks at him. “Younger siblings sure are a pain in the ass,” he growls. Dean nods in solemn agreement and Sam punches him in the shoulder. At that, Cas stands to his feet, grabs his rollaway and sticks his hand out. “It was nice meeting you.”

“Likewise,” Dean murmurs. He clasps Cas’ hand and wonders briefly what his skin feels like like under the woolen gloves.


	2. Chapter 2

He can’t be serious. “You can’t be serious,” Dean huffs a breath that he can see in front of him. In line for the lift, they are surrounded by children heading to the bunny slope and Cas is wearing a purple jacket with a black and yellow striped beanie with a pom pom on top. Dean can’t be sure, but he thinks Cas might have been flirting with him earlier and Dean also thinks he kind of liked it but he has to draw the line somewhere, and right now, it is that puffy piece of yellow fuzz on top of Castiel’s head.

“What?” Cas asks before turning his gaze back on the slow moving line. Jess chuckles at Dean and Sam is looking at him strangely and Dean cannot figure out why he’s still blushing until he looks up and sees Castiel side eyeing him from underneath his pom pom. “Jess made it for me.”

Jess breaks out into a gale of fresh giggles and Sam looks completely unsympathetic and Dean hates them all for a split second before he realizes this is the most fun he’s had since Sam moved away two years ago and decides to go with it.

“Well,” Dean begins and fuck not crossing lines, fuck his pride and fuck loneliness, most of all. “It’s cute. Great job, Jess,” Dean winks at Cas and doesn’t miss Sam’s jaw dropping before the lift is suddenly right in front of them.

“We’ll all go together once, because, if I have to go to the bunnies, so do you,” Dean says before moving forward to hop onto the moving seat. It’s slow, but they’ve been watching beginners struggle to get on the chairlift for the last twenty minutes. Now that it’s their turn, though, Cas looks absolutely green.  

Jess pats her brother on the shoulder before gently pushing him toward the chair. Dean watches with amusement as Cas digs the heels of his skis into the snow. Jess sighs and looks over at him, completely helpless and utterly annoyed.

“Thanks for going up with Cas, Dean. I learned to ski and snowboard at winter camp with friends before Cas came to live with us. I tried to teach him, but he’s stubborn and apparently, I have about as much patience as Dad,” she says. Instead of responding to the jibe, Castiel's eyes dart every which way around, looking about two seconds away from bolting back to the lodge. Without thinking too hard about it, Dean reaches back and grabs Cas’ hand and tugs him toward the lift. Jess smiles in thanks when Dean hauls him up onto the cool metal seat in front of them. She slides in next to Cas, careful not to tangle his skis with her snowboard while Sam hops on and grabs Jess’ hand. The lift jerks and sways as the four of them get comfortable and Dean releases Cas’ hand and lays a gentle arm around him, instead.

“You alright?”

Cas gives a curt nod, brow furrowed, dark hair peeking from underneath his ridiculous hat and Dean has the absurd urge to lean in for a kiss. He thinks Jess might know it too, because when Dean looks across at her, she’s staring at him like an overprotective sister who could actually, probably, at least a little bit, kick his ass.

Cas, to his credit, ignores her. Instead, he leans into Dean’s shoulder and takes a shuddering breath that causes Dean’s chest to ache a little. He’s scared and Dean knows what that feels like. He felt like that only yesterday, when the sound of Chopin’s Nocturne had been the only thing with any ability to soothe his nerves as the jumbo jet creeped up into the clouds. What he wouldn’t have given for a warm body to lean into, a steady hand to calm him.  

“Hey.” He calls Cas’ attention with a hand on the small of his back. Below them, the mountains stretch out across the horizon, covered in white, meeting the haze of the sky, opening up all around them. It’s beautiful and it’s vast. Dean loves the snow and the mountains and the feeling he gets when he drops onto the trail. He is small and insignificant in the shadow of such a powerful natural object, yet dares to challenge the mountain--to ride the sweet crunch of white all the way down to the bottom. “I’m right here.”

Cas doesn’t answer, just meets his eyes and blinks once, then twice, owlish. Dean smiles and rests his hand in the warmth of Castiel’s back. They sit that way until they reach the top of the bunny slope.

Sam and Jess mess around up top for a while so that Dean and Cas can practice parallels but Dean can tell Sam is getting restless. He encourages them to take the run and then go up to the intermediate trail on Baldy, so that they can get on with their lesson in peace.

“I don’t want to leave Cas,” Jess says stubbornly while her brother stands there reminding her that he is 38 years old, has two degrees and a cat and he isn’t a child anymore. He can take care of himself. They confer for a few minutes while Dean and Sam stand awkwardly off to the side of the flag area, where a blond, svelte Swiss ski instructor is teaching five little snow bunnies how to stand up on their skis, their mothers starry eyed and in tow.

“What are you doing, dude?” Sam asks. Dean doesn’t need clarification, but he feigns ignorance, anyway.

“Whadaya mean?”

“With Cas.”

Fuck.

“You’re flirting with Jess’ brother, Dean, come on. Don’t fuck this up for me, man. Cas just got out of a messy divorce and he’s vulnerable.”

Sam’s concern for the guy that isn’t even his brother flares up a twinge of something that feels a lot like jealousy. The Winchesters have only seen each other once since Sam left for Stanford and so of course Sam thinks he’s the bad guy.

“I’m trying to help, Sam.” Suddenly, Dean’s more annoyed than jealous. He’s not the one who asked to come up here to help Sam arrange rose petals on the sheets or babysit Jess’ brother on the bunny slope or whatever. Over the last couple of weeks, he’d been building this trip up--looking forward to helping Sam and getting to know him again. Dean gets a rush of shame and sadness at the thought that he actually believed that his brother wanted to spend time with him. “Am I embarrassing you? What could I possibly be doing wrong in your eyes right now? Cas is scared and he’s nice and I thought you actually trusted me to be around your new family, but I guess I was wrong.”

Dean tapers off his rant when he sees Cas shuffling toward them, Jess in tow. His face is closed off and Jess looks pissed, too.

“Dean…” Sam begins but Dean cuts him off with a hand.

“Sam, just go hang out with your girlfriend. It’s fine. Cas?” Dean looks at the other man, who refuses to meet his eyes. “These two are gonna give us some space. You still want me to, uh…” and just like that, Dean’s shy again, wondering why he’s fighting with his brother over this stranger. But it isn’t about Cas, not really, and Dean and Sam both know it. Unfortunately, Cas and Jess do not.

“Look Dean, I don’t think Cas is ready,” Jess says, but Castiel interrupts her.

“Yes. Let’s go, Dean. I want to,” Cas says evenly, looking at his sister. “I’m fine, Jess. I’m not a child. I’m not broken.” Brother and sister gaze at each other for a moment before Jess nods and grabs Sam’s hand.

“Let’s go, Sam.” She turns to Dean. “We’ll meet you in the clubhouse in a few hours?”

Dean nods, jaw working as he grits his teeth against the visceral response he wants to give to his uppity ass brother and his future wife. It’s not like he’s going to ravish Castiel up here on the mountain, skis and all. His brother has an outdated impression of who Dean is and it grates against every fiber inside of him. Things are so different for Dean, now that Sammy’s gone. He keeps to himself, he works his ass off at the bakery. He’d stopped visiting campus when Sam left, and he sure as hell doesn't pick up co-eds anymore. Shit, he isn’t picking up anyone, these days.

“Dean?”

He realizes it’s now just him and Cas, with three hours and an entire mountain of snow between them.

“You don’t have to, I mean, don’t want to start an argument...my sister is very protective and ever since...shit, I’m sorry, I should just...” Cas stops stammering when Dean lays a gentle hand on his shoulder. 

“I’m fine,” Dean sighs and runs a gloved hand over his face out of habit, attempting to clear his head. “How are you feeling?” he counters. “The worst part is over,” he continues, motioning to the chairlifts drifting overhead. “I always hated those as a kid, but the view can’t be beat,” he chuckles and shakes his head, sobering. “Me and Sammy, that ain’t your fault. Ever since he moved to California, things between us haven’t been the same.” Dean pokes the snow with his ski pole, digging the metal into the crunchy ice and not elaborating.

“I understand,” Cas says, voice low and solemn. “Would you like to go back?’

“No way.”

“Alright then. Would you like to teach me how to get to the bottom of this hill? Because it’s fucking cold out here.”

Dean huffs a laugh. “It’s Idaho in the middle of ski season, ‘course it’s cold. Come on,” he smiles his best shit-eating grin and pushes off with his skis to show Cas how it’s done.

Dean allows himself to forget the drama of the morning in favor of enjoying watching Cas figure his way around the terrain of the bunny slope. Cas gets the basics down quickly, and soon, they are jumping back on the chairlift to follow the sun across the mountain range. When they hit the black diamond, Dean rests a hand on Cas’ thigh and they continue on in silence until the lift returns to the lodge. It’s been more than three hours, but when Sam had called earlier, Dean and Cas had agreed that they wanted to keep going. They end up missing lunch with the family, which neither Dean or Cas can find in themselves to feel bad about.

They decide to eat together and Dean can admit, after spending most of the day with the guy, that he enjoys Cas’ quiet company. He is smart and creative--an artist--and funny, in a muted, deadpan sort of way. Dean likes him and finds himself asking about the pan pizza in Chicago and Cas’ art opening in the coming weeks not only because he’s curious but because he kind of wants to see him again. Jess had hit the nail on the head. He hasn’t dated anyone since Lisa, and he hasn’t wanted to. It’s weird, because he knows that when he sees Sam, it’s going to be all, “Dean, you’re making bad life choices,” and in the same breath, “why can’t you just settle down and find a nice person who has their shit together?” It doesn’t matter that Dean owns a kickass bakery and has two full time employees who he makes sure get paid every other week with checks that do not bounce, thank you very much. What matters is that he doesn’t feel successful, not really. In fact, he feels a bit broken. He understands why Sam told him to leave Cas alone, not because he thinks Dean is fucked up, but because _Dean_ believes he doesn’t deserve to be loved. To be fair, Dean’s track record isn’t great. There is a long list of people Dean’s fucked and then failed, and he knows it. He also knows it’s selfish of him to want Cas, knowing full well he can never be the kind of man someone would want long term. But Cas is nice and Chicago isn’t that long of a drive from Kansas City (Dean’s driven farther for Metallica tickets). Dean can’t remember the last time he had a friend to just talk to (besides Charlie) and Cas is really easy to talk to.

So easy, in fact, the two of them spend the next three days locked to each other’s side and both Sam and Jess stay blessedly quiet about the fact that they are attached at the hip. They haven’t kissed, but Dean’s been thinking about it. Boy, has he. In reality, though, he enjoys having someone besides Sam to talk to while they’re at the lodge, and so Dean and Cas spend a lot of time together, away from their siblings and Cas’ parents, on the snow, at the lodge bar (they only did karaoke once, but Dean had tried like hell every night since then to get Cas to agree to do it again) and out on Main Street. They drive to town in Cas’ rental and watch the sun go down over Bald Mountain. They ski once more, but Cas’ determination to get better is outweighed by his intense hatred of cold mornings, so they spend the other two days, just knocking around the lodge and the surrounding areas, sometimes with Jess and Sam and their parents, sometimes on their own.  They spend hours sitting by the frozen lake on the lodge property or fireside in the lobby, Cas drawing snow-capped mountains in his sketchbook, while Dean strums the strings of his guitar, neither one of them saying much and, to Dean’s surprise, it’s comfortable there, with Cas. They go ice skating and end up holding hands when Dean grabs Cas to pull him across the ice and Dean can’t help but notice the flush in Castiel’s cheeks, which he hopes is because of him and not just the freezing temperatures. They spend a late night talking, long after Jess and Sam have gone to bed, about home and heart break, and Dean starts to realize there’s more to Cas than just his funny hats and strange sense of humor. Cas tells Dean about his ex-wife, Meg, who cheated on him, then divorced him last year because he wasn’t selling any of his work, and who is now suing him for intellectual property rights to one of his gallery paintings that recently sold for $35k.

“She treated everyone else like shit, but she was always sweet to me. She made me feel special,” Cas admits over a six-pack of Sawtooth Winter Ale. “But when I had nothing to offer, she left me.”

Dean doesn’t know what to say to that, so he tells Cas about Adam. The last dude he dated, the one right before Lisa. Dean had thought he and Adam might have a future together, but Adam took a job at a New York ad agency right after graduation, citing Dean’s “daddy issues” and emotional constipation as reason enough to walk away. Dean can’t say he blames him.

“I waited too long to tell him I loved him. It was before I bought the bakery, before I knew what I wanted to do with my life. I drank too much. I was unhappy a lot of the time. He deserved better than me.” Dean continues to tick off the possible ways he fucked up that relationship until Cas rests a gentle hand on his and tells him,

“Maybe the timing just wasn’t right, Dean. Maybe you have something-- _someone_ \--better waiting for you out there,” Cas’ thumb tracing soothing circles onto Dean’s palm the entire time.

It’s comfortable and nice and completely fucked up that Dean is starting to fall for who will probably be his future brother-in-law.  


	3. Chapter 3

Dean almost forgets how transparent he is, until Bobby and Ellen arrive at the lodge.

“Well, what the hell are you waiting for, boy? A written invitation?” Bobby’s gruff voice carries across the lobby and Dean grins as he bends over to pick up Bobby and Ellen’s overnight bags.

“Glad to see you too,” Dean grunts as he pulls the old man into a hug, mostly against his will. “Hey mama,” he says, a little more shy as he gets a peck on the cheek from her. They may be his adoptive parents, but Dean’s thought of Bobby and Ellen as he and Sam’s pa and ma since before he learned to drive. He stopped begrudging them the title as soon as they opened up their home to him and his baby brother when they had no one else to turn to, and the Singers were right there. A few feet behind, Cas is shadowing him, sheepish expression almost hidden beneath his pom-pom beanie. Dean knows Ellen and Bobby have already noticed, by the way they’re both raising their eyebrows and eyeballing the stranger in the red peacoat and matching red hat.

“You gonna introduce us to your friend, Dean?” Ellen asks as she swats his hand away from her hat and coat and starts for the elevator.

“Uh, yeah. This is Cas, Jess’ brother. Cas, Ellen and Bobby Singer,” Dean waves his hand in introduction and proceeds to push them all into the opened elevator doors. Cas presses the “6” without prompting, which gets another eyebrow raise from Bobby, but he doesn’t actually say anything, which is a blessing in itself.

“So, dinner tonight with Sam, Jess and her family, am I gettin’ this right?”

“Yeah, Pop,” Dean answers, distracted by a long piece of lint hanging off the shoulder of Cas’ jacket. He drops one of the bags in his hands and picks it off, without saying a word. This earns him another raised eyebrow, this time from Ellen, who turns to Cas.

“So, Cas, is it? How do you know Dean? I thought you’d never met any of the family but Jessica, Dean,” and boy, Ellen is not subtle at all.

“Dean and I have been spending quite a bit of time together this week, partly in order to avoid familial responsibilities,” Cas answers. Dean shakes his head. Dude has no idea what he’s getting himself into.

“Cas and I have been playing ditchum on Sam and Jess,” Dean interjects at the same time Cas says,

“Mostly because I enjoy his company.”

Bobby coughs through a harsh laugh while Dean spends the last two floors up turning an alarming shade of orange. Ellen just pats Dean’s hand and smiles at Castiel.

“That’s real nice, Cas. Dean is a sweet kid. Just took him a while to get his shit together.”

“Ellen!” Embarrassment courses through him. He’d been so sure his face couldn’t get any brighter, but Dean’s always been about defying expectations, anyhow.

“It’s true, sweetie,” Ellen shrugs.

“So, uh, Sam and Jess, amirite?” Dean tries to subtly change the subject and glares at Bobby when he hears him snort from the other side of Ellen’s head. Thankfully, Cas picks up on his discomfort, and helps the topic along by offering to introduce Ellen and Bobby to his parents after they get settled in their room.

“Carol and George Moore are good people,” Cas tells the Singers as he walks them to their door. Dean hangs back, determined not to embarrass himself any more. He’s going to have a good long talk with Ellen about discussing him like he’s not even there with prospective _whatevers_ after Cas goes back to his own room.

“And we can’t wait to meet ‘em, son, but first me and my wife gotta have a nap and a talk with our boy,” Bobby motions to Dean and Cas nods, a slight smile on his lips at the term of endearment. Dean’s already told him how Bobby and Ellen raised him and Sam after their mom died and John went to jail. Much like Carol and George took in Cas, Bobby and Ellen opened up their home to both Dean and Sam when the state tried to separate them after John’s accident. Bobby and John Winchester had been in the service together and lived close enough that Bobby was in Lawrence before the sun went down the day Child Protective Services called him after John had been arrested for manslaughter while driving under the influence. The Winchester boys had been snug in two warm beds in their new room in Sioux Falls at the Singers’ home by midnight and off to school by the next Monday and not one of them had ever looked back.

“It was wonderful to meet you, Ellen. Bobby,” Cas says before pulling the hotel room door closed behind him and leaving Dean to deal with two surly senior citizens with too much investment in his love life.

“So, Sam wants us…” Dean begins before Ellen cuts him off.

“Oh, nuh uh. What is up with you and that one, Dean Winchester? And don’t you lie to me. I can always tell when you’re lying, kid, you ain’t slick,” she says as she tosses her bags onto the bed. Bobby just chuckles and shuffles into the bathroom.

“You’re on your own, son,” he says before shutting the door and allowing his wife to interrogate Dean.  

“Now, Ellen…”

“Don’t you _now_ _Ellen_ me. You like him and he likes you. But isn’t that Jess’ brother? You haven’t slept with him yet, have you?” She asks, squinting at him now, as if she could read the truth right off his face. Actually, Dean thinks, she probably could.

“No, no! Geez! What is up with you and Sam? I am not sleeping with him, Jesus Christ,” Dean huffs, flopping onto the bed and watching with relief as Ellen goes to the mini-fridge and pulls out two tiny bottles of whiskey.

“Don’t tell Pop,” she says, handing him a bottle before twisting the cap on her own and taking a slow sip. “Now, son, what are you and Castiel up to, then?”

So, while Bobby showers, Dean tells Ellen about the last week with Cas and how they’re both a little messed up, but together, it hurts a lot less. He tells her about teaching Cas to ski and Cas’ divorce. He shares that Cas hasn’t dated anyone since Meg and that Dean isn’t sure if they’re going to see each other again but he hopes that they do. He admits that he’s smiled more here, with Cas and Sam and Jess, than he has in the last two years. “I like him, yeah. And he likes me. It’s weird.”

“Why is it weird, sweetie?” Ellen asks. Bobby is taking his time in the bathroom, but he’s finished with the shower and they’re finished with their drinks.

“Because he’s so nice and he thinks I’m awesome.” Dean shrugs. “It’s weird.”

“Dean, you’re always telling me how awesome you are,” Ellen chides and Dean smiles at that.

“Yeah, but he really believes it,” he says, finally, voice soft and fragile.

“Oh, ya idjit! Would you stop pussy-footing around and make the moves on that boy, already?” Bobby hollers from the bathroom door. “You’re thirty six years old and neither one of us is getting any younger. I want some god-dang grandkids before I die of old age.”

“You ain’t going anywhere, old man,” Ellen purrs as she kisses her husband, much to Dean’s dismay.

“Oh, come on, I’m sitting right here,” Dean grimaces and jumps off the bed, face scrunched up in mock disgust.

“Then you better get outta here so me and your mama can have at that nap,boy,” Bobby says.

“Is that what the kids are calling it these days, oldtimer?” Dean laughs and kisses Ellen on the cheek. “Thanks,” he whispers. She wraps an arm around his waist and squeezes.

“You deserve a little happiness, sweetheart,” Ellen replies, voice low. It makes Dean flush with pride.

“Alright, you two, I’m going. But you two better be downstairs by six,” Dean reminds them and shuts the door quick enough to miss the shoe that hits the door with a thump.

“Ya idjit,” Bobby mutters from the other side of the wood.

Dean doesn’t have time to freak out about Cas because he’s too busy saving Sam from freaking out about proposing to Jess. The younger Winchester had come to Dean’s door about an hour before dinner, and hasn’t stopped pacing the floor since.

“Sam,” Dean blurts out, after watching his brother wear a track in the carpet from walking back and forth about seven hundred times in a row. “Why are you so freaked out? It’s gonna be great, everyone’s had such a great time this week. You done good, son,” Dean jokes, but Sam’s returning smile looks more like a grimace. “Seriously, Sam.” He’s getting a bit desperate here. Sam’s usually the level-headed one, able to rationally think his way out of and into any type of situation. “The Moores love you. Jess loves you. Bobby and Ellen are gonna love Jess.” Dean pats the bed next to him, inviting his brother to sit down. Sam does, but he’s still jittery, leg bouncing up and down, causing the entire bed frame to shake. “Come on, kiddo, tell Dean what’s wrong.”

Sam turns a vicious glare on Dean, which briefly causes him to rethink his life choices, but the glare soon simmers into a pitiful frown that makes Sam look like he’s about twelve years old. “She’s too good for me, Dean,” he says after a stretched out silence.

“Aw, come on, Sasquatch, don’t talk like that,” Dean teases but sobers when he sees the look on Sam’s face.

“I’m not joking Dean, she’s a fucking saint,” Sam insists. “She’s a straight A student, she volunteers every week at the local women’s shelter near the college, she works two jobs so that her parents don’t have to pay for more than her books, she hardly ever drinks. Dude, she has two rescue cats,” he says looking up at Dean, eyes wide. “And she’s never even smoked pot, let alone anything harder,” he finishes and Dean finally begins to understand. “What the hell is she doing with an addict like me?” He asks, choked up and unable to hold back the tears any longer. “I’m afraid I’m gonna fuck her up, ya know?”

And yeah, Dean knows.

“Sammy, you kicked that shit. You beat it. She knows that and she still loves you. You!” Dean punctuates the word by punching Sam in the leg. His brother sniffles but smiles through it and that’s exactly the opening Dean has been waiting for. He thinks of Ellen’s words to him and shakes his head in disbelief. Goddamn Winchesters and their self-sacrificing tendencies. “You deserve to be happy, Sam, after what you’ve been through and what you overcame. Jess loves you in spite of the fact that you’re an ex-junkie and you’re not going to ruin anything. You’ve got to ask her. You’ve got to find out if she wants to be with you and go through all this,” Dean waves his hand to the signify. “This wonderful, weird bullshit we call life, together.” He doesn’t finish as strong as he would like, but it’s been a long week and he thinks he’s finally starting to understand what Ellen had been telling him earlier. About him and Cas.

Sam takes a deep breath and turns to face Dean. “And what about you? Are you happy? Don’t you want to share all this,” he waves his hand, mimicking Dean. “With someone?” And there’s the kicker. Yes, Dean does, but...it’s complicated.

“It’s complicated?” Dean answers, voice lilting up at the end as if he’s asking a question.

Sam snorts. “It’s always complicated.” He takes a deep breath, smooths out invisible creases in his pants and looks at his brother. “Thank you, Dean.” He rushes on before Dean can interrupt him. “Seriously, man. For everything. For a long time. You came out, you always come out.” It’s Dean’s turn to snort. “You know what I mean,” Sam rolls his eyes and Dean is happy to note that thoughtful, self-destructive Sam has been replaced with the long-suffering little brother mode Dean’s come to cherish. “For me. You’ve been there for me through all of it and I,” he clasps Dean’s shoulders and Dean suddenly feels very close to tears, himself. “I appreciate that even when I didn’t believe in me, you did. And I need you to know that I’m proud of the man you are, Dean. You’ve got the bakery and you’re doing really good for yourself back in Kansas, but I know you’re lonely. Even though you’ve got Charlie and Benny, I can tell. Even more so because of this week.” Dean stiffens. He doesn’t want to get into it with Sam. This thing he has with Cas, it’s too confusing, too new. Even he and Cas are still dancing around it, careful not to upset the balance of the tightrope they’re walking on. There are so many things that could go right but also so many ways he could fuck this up. Dean knows he’s never been this serious about anyone, not even Lisa, and they’d lived together.

“I don’t,” Dean begins, shaking his head.

“I know, I know. You don’t want to talk about it. I’ll enable your horrible communication skills, for now.” Sam says as he stands and takes a quick peek at his phone. “It’s ten ‘til, anyhow, time to go. I just,” he stops, hand on the door handle. “You and Cas make each other happy and you both deserve something good in your lives.”

Dean sucks in a breath and closes his eyes before standing to his feet and clearing his throat. “That’s...that means a lot and, well, you too, baby brother. I’m proud of you, Sammy,” he says, voice gruff even to his own ears. “Proud of us,” he finishes, placing a hand on Sam’s shoulder and squeezing. “Thank you.”

The silence is overwhelming, but then Sam huffs, shakes out his mane and runs his fingers through it, and steps into the hallway. “Let’s do this, Jerk.”

“Come on then, Bitch.”

Sam had reserved the back of the Lodge restaurant for their party of eight and the staff (along with Sam, Dean and Cas) spent the afternoon transforming the room into a winter wonderland. There are fairy lights and paper chains draped across the ceiling that Cas and Dean had worked on in the lobby for hours the night before, getting help from curious and friendly hotel patrons, until the precise measurements were met. The long, wooden table is covered with the restaurant’s signature white china and a simple white cloth, dishes piled high with cheeses and fruits and nuts. Mini pies, that happen to be the chef’s specialty, fill in all the free space and it takes all of his will power for Dean to sneak only one tiny apple concoction off the table before Sam catches him and tells him to stop. Dean decides he’s going to eat one of each flavor, and Cas, who is sitting next to him at dinner, agrees that the idea is a good one, and promises to do the same. In the middle of the table sits a bouquet of burgundy roses and baby’s breath, the vase surrounded by tealights, atop a mirrored surface. The candles and the mild brightness of the fairy lights give the room a gentle glow and under the murmur of voices as the first course of spicy tortilla soup is set before them; Dean thinks Sam and Jess look really, really happy.

Jessica, George and Carol Moore, Castiel Novak, Bobby and Ellen Singer and Dean and Sam Winchester sit around the table for a good hour before Sam works up the nerve to call the table to attention by clinking his dessert fork against his green glass bottle of Perrier.

“Aherm.” Sam clears his throat, and Dean tries to school his expression when Jessica looks over at him, then Cas, eyebrows raised, silent question on her lips. Ellen and Carol are glancing at each other and their husbands, and it’s all Dean can do to not grin or to rib Sam, knowing he’s the only person (besides Cas, who figured it out pretty quickly after Dean begged for his help with the paper chains and fairy lights) who saw this moment coming.

“I’d like to say something, guys, please?” Sam implores his family and the room settles down, all eyes on the younger Winchester. Sam turns to Jess, and Dean is watching her too, now. Her eyes are shining with unshed tears, and her left hand covers her mouth. She’s sitting on the other side of Castiel, and Dean can see her grab his knee and squeeze, which makes it really hard to keep a straight face, knowing her joy matches Sam’s.

“Jessica Moore,” Sam begins and Ellen is already wiping tears from her eyes across the table from Dean, which causes a lump to form in the back of his throat as he looks between his brother and the two women who Sam loves most on this earth. Sam never met Mary Winchester--she died when he was a baby, before Sam could get to know her smile or the songs she would sing to the brothers to get them to go to bed at night. Ellen, for all intents and purposes, is Sam’s mother, Dean’s too, but the elder Winchester still remembers Mary, like one remembers a dream, faded and fuzzy, but fond. For Sam, though, it is different. Ellen is the one who bandaged their cuts and scrapes, attended their graduations and games, cooked holiday dinners and made them do their chores every time they spent time in her house, even now. Sam had tried so hard to sever his familial relationships with not only Dean and their friends back home, but with the Singers, as well, when he was hooked on the pills. He cursed, blamed, coerced and pushed away each and every person who cared about him, until Ellen showed up on his doorstep, all the way in California, with Bobby and Dean, to hold an intervention and drag his ass to rehab. If it weren’t for Ellen’s care and guidance, that motherly instinct that made her fearless in her attempts to save Sam’s life, he might not be standing here right now, getting ready to propose, with sweat beading across his forehead, surrounded by all those that he holds so dear.

“When we first met, I was only a few months sober and a complete and utter asshole.” The table skitters with laughter and Sam grimaces, tucking his chin into his chest and looking up through his lashes to the people at his table. “Seriously, you all know how I was back then, and Jess, well, she allowed me into her life, and changed me forever,” he says, voice unwavering. “I love you, I need you, and I want you by my side Jess, from now until always. If you’ll do me the honor of being my wife, I’ll spend the rest of our lives showing you just how much you mean to me.”

Dean grins at the collective gasp from the room as Sam slides down to one knee and pulls a black, velvet ring box from his pocket. He’s the only person who has already seen the ring--a bright, vintage piece from an antique gallery that took Sam two months to save up for, and, gauging Jess’ reaction to a ring she only mentioned once in passing to her boyfriend, who went back, bought it, and is now down on one knee, he thinks Sam must have done good. The future Mrs. Winchester hops up and tugs Sam to his feet, gathering all six plus feet of him in her arms, murmuring, “Yes...yes…” into his neck, to a burst of applause from their family. Dean stands to his feet in a wave of pure joy, so proud of his baby brother he feels like his chest is going to burst. In that moment, he catches a glimpse of Cas that takes his breath away. The other man wears a mild smile on plush, pink lips, watching the scene with open affection. His eyes shine in the twinkling fairy lights they helped string up, dark hair looking as if he’d tried to run a comb and gel through it, but ended up running his fingers through it, instead. The blue tie hanging around the neck of a simple, white dress shirt matches his eyes and watching Cas clapping, smiling, joking with his mother and genuinely happy, Dean can’t help but think that Cas is the most beautiful thing he’s ever seen.

“Beautiful,” Dean breathes, voice full of awe, and he’s not sure if he means the proposal or Cas, who turns to him and smiles, a dazzling smile that Dean want to kiss off of him. Meeting his eyes, Cas repeats,

“Beautiful.”

Yeah. Dean definitely means Cas, and he really, really wants to kiss him.

After the words of encouragement and teasing, dessert and coffee, the Moores and the Singers head back up to their rooms, promising to rise early and hit the slopes with the entire group the next morning. Sam, Jess, Dean and Cas stay up for a while, chatting over beers and a hockey game on the television at the bar. Jess ponders the well-known fact that Sam is horrible at keeping secrets from her, and probably had a helluva time hiding the proposal over the last week from her. Dean commiserates completely, and regales them with tales of Sam’s jittery nervousness over the last five days that have Jess and Cas snorting and poking fun of Sam in a good-natured way. When Dean catches Jess staring at his brother like Sam hung the moon for the tenth time that night, he orders them upstairs, to which they comply easily.

“How about you?” He asks Cas, finally. They’re alone in the lobby, save the bellhop and the older gentleman working the desk for guests arriving after hours. “You ready to call it a night?”

“Not quite,” Cas answers, reaching across to clasp Dean’s hand in his own. Dean watches Cas’ trace a line across his knuckles, feels the pad of his thumb soft against Dean’s skin as their fingers entertwine. “I’m not ready for this week to end, if I’m being honest. I’ve...I’ve enjoyed our time together.” Cas has his eyes cast down, looking at their joined hands and Dean takes the moment to map the contours of his face, the slope of his nose, the strict line of his jaw, the stubble collected there over the course of the last day or so. Cas’ face is smooth and contemplative now, but Dean knows, when he laughs, he gets these ridiculous crinkles in the corners of his eyes that make his entire face light up. Dean longs to reach out and touch, but he isn’t sure whether he should. He doesn’t want to push and he certainly doesn’t want to rush what he’s got here, with Cas. It seems too delicate; a fragile thing that he doesn’t want to barrel into, like he usually would.

“Ever since Meg and I…” Cas doesn’t finish the sentence, but Dean understands. “I’ve felt lost; as if I’m wandering through life, missing something. I work, I see friends and family, but it all feels so hazy. So...empty. It’s been a year since she filed those divorce papers, but I’m still not sure what I’m supposed to be doing. I thought we would be together forever. I thought she loved me for me and now, I’m not sure who I am anymore.” Cas stops and looks at him. “Jess thinks I’m broken,” he admits in a low voice. “And I’m not sure she’s wrong.”

“Sam thinks I’m a lost cause.” Dean offers with a wry smile. “That I break everything I touch.”

“Well you can’t break someone who’s already broken,” Cas states.

“You’re not broken, Cas. You’re amazing! You’re funny and sweet and thoughtful and a good brother and son. You’ve been through the ringer, but here you are, on the other side, getting ready to show your art at a real gallery, to watch your sister walk down the aisle. It’s just different now. You’re different.” Dean sits up straight, but doesn’t let go of Cas’ hand. “I think that it’s okay to lose stuff. For things to end, ya know?”

Cas doesn’t answer, just tilts his head and watches him, so Dean plows forward.

“Because when we lose things, when relationships come to an end or jobs or whatever, it makes space for something even better. Something new.”

“Like us.”

Dean’s breath catches in his throat. “Yeah, Cas. Like us.” He leans forward and rests his forehead against Cas’, sharing space and breath, hands still clasped tight. It’s more intimate than anything Dean has done with another person in a long time and he aches with how much he wants to see Cas smile, to watch the wrinkles on the side of his eyes to form. “I’d like to see you again,” Dean says, finally, pulling back to look Cas in the eye. “I can head up to Chicago?” He forms the statement as a question, ready for rejection. Ready to back off, retreat, if necessary. But Cas doesn’t let him off that easily.

“My gallery opening is in a month. Come.”

Dean immediately thinks of eight reasons why he can’t attend. It’s short notice (not really), he’s got the bakery to worry about (Charlie can handle things), he hardly knows the guy (he might already be a little bit in love with him), Chicago is too cold (Kansas is cold, too), he hates to fly (true) and shouldn’t drive the Impala in the snow (also true), he’s never been an _art gallery_ type of guy (but he loves Monet, shuddup), and, the biggest most looming reason of all, **he’s definitely going to fuck this up**.

“Dean?”

Cas is looking at him, waiting for an answer and Dean wants to say nevermind, that he can’t, he won’t, he shouldn’t. Instead, he sighs, a small smile tugging at the corners of his mouth. “Yeah. I’d love that.”

“Really?”

“‘Course. Was waiting for you to ask, anyhow. I’m dying to see these paintings of yours,” he says, eyes catching on the way Cas licks his lips before he speaks.

“Dean?” Cas murmurs, leaning in close once again.

Yeah?”

“I’m going to kiss you.”

_Oh._

Cas places his hand against Dean’s jaw and moves in to press a chaste, close mouthed kiss to Dean’s lips. It’s sweet and short and Dean immediately wants more. He doesn’t take, instead he is patient, and boy, is it worth the wait. Cas licks into his mouth, and everything that Dean knows about Cas is confirmed in a single kiss. Running his tongue across Dean’s teeth, Cas explores without hesitation, snaking his arm around Dean’s neck to reel him closer. With his fingers caressing the nape of Dean’s neck, Cas kisses him and all Dean can think of is that he hopes this is the first of many and _damn_ , Cas can kiss. When he pulls back, Cas’ eyes twinkle in the dim light and his lips look swollen and well kissed. Dean is still staring at Cas’ mouth when the corners tilt into that gummy smile he has come to associate with snowy days and bad bee jokes and a resilience that gives Cas the strength to push forward even when he isn’t sure he can or even should.

“I liked that,” Cas whispers, his warm breath ghosting across Dean’s lips causing him to shiver.

“Me too.”

“I should go to bed.”

“Me too.”

Without another word, Cas rises to his feet and holds out a hand to Dean. They walk to the elevator and inside, they press close, but don’t kiss again. At the sixth floor, Dean walks Cas to his door, but doesn’t ask to come in. Instead, he kisses Cas on the forehead and watches him head inside and shut the door before turning to his own room. Inside, Dean kicks off his dress shoes and unbuttons his dress shirt before nestling down deep under the thick comforter. In the dim light of his hotel room, Dean maneuvers his phone into the speaker jack, a familiar legato notes of violin and piano drifting through the air, soothing him into sleep, where he dreams of snow and blue eyes and shining smiles underneath fairy lights.

When Dean wakes up the next morning, he’s well rested like he hasn't been in years. The entire family heads to the airport together, flights staggered throughout the day, sending them one by one into different terminals and different parts of the country, most of them not to meet again until Sam and Jess’ upcoming wedding, which, of course, has no set date. Sam and Jess’ flight to California leaves last, right before Castiel’s, and so it's a little awkward when Dean says goodbye to Cas under their watchful gazes. No one had said a thing when Dean and Cas been caught holding hands under the table at breakfast, but Jess did corner him in the lobby gift shop (he had promised Charlie an authentic Idahoan souvenir and ended up getting her a figurine of a moose on a snowboard that reminded him of Sam, for some reason), to threaten him, in proper sibling fashion.

“I like you, Dean, and I love Sam, but if you so much as think about hurting my brother, I will salt and burn you and they will never find your remains.”

He nodded, looking (he hoped) and feeling (without a doubt) appropriately terrified. Still, the earlier encounter with such a formidable opponent causes Dean to rethink his airport goodbye strategy and go for a hug and innocent cheek peck when his nonstop to Kansas starts to board.

“I'll see you soon,” he murmurs, lips buried in Castiel’s hair.

“You will.”

It isn't a question, and Dean smiles against the collar of Cas’ red peacoat, squeezing once more before he lets go and turns to hug Jess and his brother. Sam smiles a dopey grin at him that has Dean rolling his eyes and swearing to never visit again unless Sam quits the chick flick moments, which, both of them knows, will never happen on either one of their ends. He kisses Jess on the cheek and then gives Cas one more smile before handing off his ticket to the flight attendant. With his guitar slung over his shoulder, Dean pushes through the line of people toward his seat on the plane. His nerves buzz because he hates to fly, yes, but this time, it's more than that. Anticipation of the future--of visiting Chicago and spending time with him at Sam’s wedding, of seeing Charlie and Benny and telling them about his time in Idaho--zips through him. It feels good and somewhat scary, but ultimately, it feels like hope.

**THE END**


End file.
